Aliphatic Sulfonyl Fluoride Synthesis via Fluoroalkylfluorosulfonylation of Unactivated Olefins under Photoredox and Palladium Dual Catalysis

doi:10.6023/cjoc202604031

Chinese Journal of Organic Chemistry

ARTICLE

光氧化还原/钯协同催化未活化烯烃氟烷基氟磺酰化合成脂肪族磺酰氟

彭莹莹, 张超艺, 伍雄, 刘忍, 庞婉, 马晓玉^*, 刘超^*

上海应用技术大学化工与能源技术学部,上海绿色氟代制药工程技术研究中心,上海 201418

收稿日期:2026-04-22 修回日期:2026-05-13
基金资助:
国家自然科学基金(No. 22471172)资助项目.

Aliphatic Sulfonyl Fluoride Synthesis via Fluoroalkylfluorosulfonylation of Unactivated Olefins under Photoredox and Palladium Dual Catalysis

Yingying Peng, Chaoyi Zhang, Xiong Wu, Ren Liu, Wan Pang, Xiaoyu Ma^*, Chao Liu^*

Faculty of Chemical and Energy Technology and Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai Institute of Technology, Shanghai 201418, People' s Republic of China

Received:2026-04-22 Revised:2026-05-13
Contact: ^*E-mail: chaoliu@sit.edu.cn
Supported by:
National Natural Science Foundation of China (No. 22471172).

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Abstract

Both fluoroalkyl and fluorosulfonyl groups are important structural motifs in bioactive molecules and valuable functional units in synthetic chemistry. Herein, we report a photoredox- and palladium-dual-catalyzed fluoroalkylfluorosulfonylation of unactivated olefins using aryl trifluoromethyl compounds as fluoroalkyl radical precursors, 1,4-diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct (DABSO) as the sulfur dioxide source, and N-fluorobenzenesulfonimide (NFSI) as the fluorine source via radical sulfur dioxide insertion and fluorination strategy. This transformation enables the simultaneous installation of fluoroalkyl and fluorosulfonyl groups across carbon-carbon double bonds in a single step, thus providing an efficient and concise approach to structurally diverse aliphatic sulfonyl fluorides. The reaction proceeds under mild conditions and exhibits good functional-group tolerance. Furthermore, the resulting sulfonyl fluoride products can be readily transformed into valuable compounds through SuFEx reactions.

Key words: fluoroalkylfluorosulfonylation, sulfonyl fluorides, alkene difunctionalization, photoredox/palladium dual catalysis

Cite this article

Yingying Peng, Chaoyi Zhang, Xiong Wu, Ren Liu, Wan Pang, Xiaoyu Ma, Chao Liu. Aliphatic Sulfonyl Fluoride Synthesis via Fluoroalkylfluorosulfonylation of Unactivated Olefins under Photoredox and Palladium Dual Catalysis[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604031.

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光氧化还原/钯协同催化未活化烯烃氟烷基氟磺酰化合成脂肪族磺酰氟

Aliphatic Sulfonyl Fluoride Synthesis via Fluoroalkylfluorosulfonylation of Unactivated Olefins under Photoredox and Palladium Dual Catalysis

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